Boc-L-Met-OSu

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP25820

CAS No:3845-64-5

Synonyms/Alias:Boc-Met-OSu;3845-64-5;Boc-L-methioninehydroxysuccinimideester;C14H22N2O6S;TBM-NHS;15461_ALDRICH;SCHEMBL8614577;15461_FLUKA;MolPort-003-926-807;ZINC1579824;4979AB;AKOS016003076;Boc-L-methioninehydeoxysuccinimideester;N-Boc-L-methionineN-SuccinimidylEster;AK-81135;KB-281503;B3433;FT-0698357;LT00645688;ST24030210;N-(tert-Butoxycarbonyl)-L-methionineN-SuccinimidylEster;2,5-Dioxo-1-pyrrolidinylN-{[(2-methyl-2-propanyl)oxy]carbonyl}methioninate

Chemical Name:N-alpha-t-Butyloxycarbonyl-L-methionine succinimidyl ester

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cGMP Peptide
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  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C14H22N2O6S
M.W/Mr.
346,39 g/mole

Boc-L-Met-OSu is a Boc-protected L-methionine N-hydroxysuccinimide ester (OSu), combining an acid-stable amino acid precursor with an activated carboxylate for efficient amide bond formation. This functionalized amino acid derivative is widely used as a peptide coupling reagent building block in peptide synthesis workflows and as a reactive intermediate for preparing methionine-containing amide linkages under controlled conditions. The Boc group supports compatibility with protected-amino-acid assembly strategies, while the OSu ester enables downstream condensation to form peptide bonds or related amide conjugates.

1. Peptide Coupling Building Block

Boc-L-Met-OSu is frequently selected for peptide synthesis and segment coupling where methionine incorporation is required with the carboxyl group pre-activated as an N-hydroxysuccinimide ester. Researchers performing solution-phase peptide assembly use this activated form to streamline amide bond formation with appropriately protected amine partners, improving operational convenience compared with generating activation in situ. Because the amino group is protected as Boc, the reagent is commonly handled as a defined, single-purpose methionine building block for constructing methionine-containing sequences and intermediates in custom peptide manufacturing and research peptide libraries.

2. Methionine Amide Intermediate Synthesis

Boc-L-Met-OSu is also used to prepare methionine-derived amide intermediates for medicinal chemistry and chemical biology programs that require controlled installation of a methionine moiety into larger scaffolds. In these workflows, the OSu ester provides a reliable activation state for coupling to amines, enabling the rapid generation of Boc-protected methionine amide products that can be further transformed into targeted peptide-like structures, side-chain-modified analogs, or coupling-ready intermediates. The defined stereochemistry of the L-methionine backbone supports consistent structure control in downstream SAR-focused synthesis and intermediate development.

3. Protected Methionine Linker Formation

Boc-L-Met-OSu supports the construction of protected methionine linkers used in the preparation of modular conjugation-ready fragments for research-grade materials and biomolecule labeling strategies. Synthetic chemists often rely on the OSu activation to form amide linkages with primary or suitably protected amine-containing partners, while retaining the Boc protection to manage chemoselectivity during multi-step assembly. This makes Boc-L-Met-OSu useful when methionine-containing linkers must be introduced as defined building blocks, for example in the stepwise construction of peptide conjugates, affinity reagents, or other amide-linked molecular architectures used in chemical biology and biomaterials development.

Size
25 g;
InChI
1S/C14H22N2O6S/c1-14(2,3)21-13(20)15-9(7-8-23-4)12(19)22-16-10(17)5-6-11(16)18/h9H,5-8H2,1-4H3,(H,15,20)/t9-/m0/s1
InChI Key
PCZJWSPKNYONIM-VIFPVBQESA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCSC)C(=O)ON1C(=O)CCC1=O

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